How DO you draw different office workers?

Unit One: Thumbnails

My character's name is simply "J."  As the description on the image says, " 'J' is a cubicle monkey in her mid-20's.  She hates her job but puts up with it anyway.  She has terrible anxiety, especially around her boss and coworkers."  Drawing fantastical characters is fun, but I wanted something challenging (and something that I could use later on).  I still have no idea on how to make different "office"-type characters, but I tried my best.  I figured that this project would be hard, but I hadn't realized how I've been drawing the same way for so many years now that doing something different is like trying to write with my right hand.  It's awkward and difficult, but I am seeing progress (since this is thumbnail attempt number 2).  Thumbnail attempt number 1 was a disaster!  But that's why I'm doing this class--to learn other ways of approaching art.  Thank you, Charlie!

Unit Two: Refining

So I picked the 4 thumbnails above and I've started to refine them.  It was initially harder to pick just a few than I thought it would be, but overall, it wasn't too terrible.  Some of them were outright bad--others just didn't convey what I'd written for the character description. 

Unit Three: Variations

I decided on the first of the four poses above because it felt the most like the character I was trying to create.  Which is funny, actually, because initially it was one of the poses I liked least.  For my variations, I decided to try different outfits and styles of headphones. 

I like all of them for different reasons, but I think the third one is too polished/pretty for the character I want.  The first two are pretty good, though. 

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